I started bartending because I though it would give me a great opportunity to get laid. From all of the stories I have ever heard bartenders seem to get the most action, maybe I got the idea from watching "Cheers." Anyway I was a senior in college and had plenty of action with the sorority girls, but wanted to get with some more mature women and experience new things.
I had been on the job for about a month and noticed that there was one woman who came in all of the time. I knew what she liked and always had her drink poured before she even sat down. She frequently the most stunning outfits that seemed to cling to her figure. She had beautiful 36d tits that screamed to be freed from the tight clothing; she was about 5'9'' and always wore the highest of heels and the shortest of skirts to show off her long legs.
After a month of her coming into the place I noticed that she turned everyone down no matter what their line was or what they looked like. My curiosity got the best of me one day and I started having more of a conversation with her then just the usual. "What'll you have?" I asked her what she liked about his place since she was not looking to hook up whenever I saw her. I just re She coyly replied back that she was looking for someone to, "hook up" with and smiled at me as she made the quote signs. Embarrassed for acting immaturely I blushed. She went on to say that she was just waiting for me to approach her. I asked her," Why?" and she told me, "I'm just following orders."
I looked at her confused and she shook her head saying, "Don't worry about it." She then asked if I would like to come to her apartment after I got off work. I tried to stay cool and reply yes, but I'm sure it came out like a schoolboy overly anxious about his first time. In a lot of ways this would be my first time not only with an older woman, but now as I look back I realize that I was still very inexperienced in many ways. The rest of the night I battled with my hard on unable to control my thoughts about what I was going to get later that evening. I wasn't even close.
She waited at the bar until it closed and drove me to her house, we shared small talk while I continued to try and hide my hardon, which was pretty impossible now that I had my apron off. She told me her name was Brandi and had been scoping me out from the first night she had walked into the bar. She then smiled at me and began rubbing my 8" cock through my pants telling me it wont be long now.
When we arrived at her apartment, which was more like a loft, one huge area with the bed right in the middle. She kissed me and told me to take my cloths off and wait on the bed. I stripped quickly as she went into the bathroom and jumped on the bed. Being so anxious about what I thought was coming up the black silk sheets and candles never clued me in what she was into, but when she walked out of the bathroom in a white leather bra and panties I began feeling like I had no idea what I was doing. I've never been into the whole D/s thing, but was about to get a valuable lesson that opened my mind to a wonderful option when it came to sex.
When Brandi asked me if I had ever been tied up, I giggled as I said no. She smiled as she instructed me to lie on my stomach. She then chained each of my arms and legs to the four corners of the bed. The chains were long enough to allow some movement, but I felt extremely anxious realizing I was totally in her control. She then grabbed a black silk scarf and asked if I new what it was for. When I said No she laughed as she blindfolded me. My mind was racing, here I was lying on my stomach not able to see anything or free myself, this was already the most exciting sex I had ever had and we had not even really done anything yet.
Brandi told me to relax and that I would have the most intense experience I had ever dreamed about. I took a deep breath and waited for her to do whatever it was she was going to do. Then out of nowhere I heard her say, "Did I do good Sir." I was about to respond when I heard another voice in the room say, "Yes slave you did very well." I was terrified; there was another man in the room while I lay there naked and helpless. He then went saying, "You, are now my slave as well. You will refer to me as Sir and will follow all of My directions. Do you understand?"
I was terrified. I couldn't speak. All of the sudden SMACK, I yelled out in pain as my bare ass was spanked my by what felt like the biggest paddle in the world. I heard him ask me again if I understood and I cried out "Yes." SMACK, I was spanked again this time even harder. A tear fell from my eyes as I screamed "Yes Sir!"
Even though the spanking was extremely painful I also felt a shiver all over my body, I could feel that my cock was as hard as ever under me, and I realized that I was getting even more excited. Now I know why those Frat boys like paddles so much.
